Xrimethylsilylphenoxy esters



Reissued May 12, 1953 TRIMETHYLSILYLPHENOXY ESTERS John L. Speier, Jr.,Pittsburgh, Pa., assignor to Dow Corning Corporation, Midland, Mich., acorporation of Michigan No Drawing. Original No. 2,584,752, datedFebruary 5, 1952, Serial No. 205,032, January 8, 1951. Application forreissue February 3, 1953,

Eerial No.- 334,988

4 Claims. (Cl. 260-4483) Matter enclosed in heavy brackets appears inthe original patent but forms no part of this reissue specification;matter printed in itali s indicates the additions made by reissue.

where R is a monovalent hydrocarbon radical and R is a methyl radical orhydrogen.

These compounds may be prepared by reacting a chlorosilane of theformula RsSiCl with an alcohol of the formula CICBH-iOCHZCHR'OH- Thelatter are commercially available products sold under the name Dowanol.The reaction proceeds at room temperature or above and is preferablycarried out under anhydrous conditions and in the presence of a hydrogenhalide acceptor such as pyridine or ammonia. Forgthe purpose of thisinvention R may be any monovalent hydrocarbon radical such as alkyl,phenyl, alkylene, alkaryl, naphthyl, or alkines.

The following examples are illustrative only of this invention andshould not be construed as limiting the scope thereof. The scope of theinvention is set forth in the appended claims.

Example 1 232 grams of l-p-chlorophenoxy-Z-propanol was dissolved in 200m1. of dry toluene along with 99 grams of dry pyridine. 150 grams oftrimethylchlorosilane was added slowly with shaking and cooling.Pyridine hydrochloride precipitated and was removed by filtration. Thereaction product was IJ-CICBHAOCHZCH(CH3) OS1(CH3) 172.5 grams of2-,(p-chlorophenoxy) ethanol was dissolved in 400 m1. of toluene. 120grams of trimethylchlorosilane was added and the mixture was heated toC., at which temperature H01 was evolved steadily for three hours. Themixture was cooled and anhydrous ammonia was bubbled through the mixtureuntil the odor of ammonia persisted. Ammonium chloride, was thenfiltered from themixture and the filtrate was distilled. 195 grams of2(p-ch1orophenoxy) ethoxytrimethylsilane p-c1csmocrncrnosucm) a wasobtained. This compound had a boiling point of 166 C. at 29 mm., rl1.4928, di 1.061,

and a specific refraction of .2738.

Example 3 172.5 grams of 2(o-chlorophenoxy)ethanol was reacted withgrams of; trimethylchlorosilane in accordance with the precise procedureof Example 2. The resulting product waso-chlorophenoxyethoxytrimethylsilane,

o-cicamocinomosi (CH3) 3 This material has a boiling point of 158 C. at26 mm., n 1.4948, d; 1.066, and a specific refraction of 0.2735.

That which is claimed is:

l. A compound of the formula [RzSiOCHzCHR'OCBI-RCI] RsSiOCH RCHzOCaH 4C1where R is a monovalent hydrocarbon radical and R is selected from thegroup consisting of methyl radicals and hydrogen.

2. -clcemocmcmorn) OS1(CH3) a.

3. p-C1CaH4OCI-I2CH2OSi(CH3) a.

JOHN L. SPEIER. .111.

No references cited

